EP1345493B1 - Melanges fongicides se basant sur des composes d'amide - Google Patents

Melanges fongicides se basant sur des composes d'amide Download PDF

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Publication number
EP1345493B1
EP1345493B1 EP01271095A EP01271095A EP1345493B1 EP 1345493 B1 EP1345493 B1 EP 1345493B1 EP 01271095 A EP01271095 A EP 01271095A EP 01271095 A EP01271095 A EP 01271095A EP 1345493 B1 EP1345493 B1 EP 1345493B1
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EP
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Prior art keywords
formula
set forth
compounds
halogen
amide compounds
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
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EP01271095A
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German (de)
English (en)
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EP1345493A1 (fr
Inventor
Karl Eicken
Arne Ptock
Eberhard Ammermann
Reinhard Dr. Stierl
Gisela Lorenz
Siegfried Strathmann
Maria Scherer
Klaus Schelberger
Manfred Hampel
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BASF SE
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BASF SE
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Application filed by BASF SE filed Critical BASF SE
Priority to SI200130458T priority Critical patent/SI1345493T1/sl
Publication of EP1345493A1 publication Critical patent/EP1345493A1/fr
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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings

Definitions

  • the invention relates to methods for controlling Harmful fungi with mixtures of compounds I and II and the use the compounds I and the compounds II for the preparation such mixtures.
  • the present invention mixtures were the object of the at reduced total amount of applied drugs have an improved action against harmful fungi (synergistic Mixtures).
  • the mixtures according to the invention act synergistically and are therefore to control harmful fungi and in particular true ones Mildew fungi in cereals, vegetables, fruits, ornamentals and vines particularly suitable.
  • formula I represents compounds in which R 1 is in the 2-position and R 2 is in the 4-position (formula I.1):
  • R 1 is halogen, in particular chlorine and R 2 is tolyl, in particular p-tolyl.
  • the compound of the formula IIa (common name: cyazofamide) is particularly preferred. It is known from EP-A 298 196.
  • Halogen is fluorine, chlorine, bromine and iodine.
  • X is bromine (IIb.1) or chlorine (IIb.2) stands.
  • the compounds II are due to the basic character of in nitrogen atoms containing them, with inorganic or organic acids or with metal ions salts or adducts to build.
  • inorganic acids examples include hydrohalic acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide and carbonic acid, sulfuric acid, phosphoric acid, nitric acid.
  • organic acids for example, formic acid and Alkanoic acids such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid and glycolic acid, thiocyanic acid, lactic acid, Succinic acid, citric acid, benzoic acid, cinnamic acid, Oxalic acid, alkylsulfonic acids (sulfonic acids with straight-chain or branched alkyl radicals having 1 to 20 carbon atoms), arylsulfonic acids or -disulfonic acids (aromatic radicals such as phenyl and naphthyl bearing one or two sulphonic acid groups), Alkylphosphonic acids (phosphonic acids with straight-chain or branched Alkyl radicals having 1 to 20 carbon atoms), arylphosphonic acids or diphosphonic acids (aromatic radicals such as phenyl and naphthyl bearing one or two phosphoric acid residues), where the alkyl or aryl radicals can carry further
  • the metal ions are in particular the ions of the elements of first to eighth subgroup, especially chromium, manganese, iron, Cobalt, nickel, copper, zinc and next to the second main group, especially calcium and magnesium, the third and fourth main group, in particular aluminum, tin and lead into consideration.
  • the Metals may be present in different cases Valences exist.
  • the mixtures of the compounds I and II or the compounds I and II applied simultaneously, together or separately, are characterized by an excellent effect against a wide Spectrum of phytopathogenic fungi, in particular from the Class of Ascomycetes, Basidiomycetes, Phycomycetes and Deuteromycetes out. You are currently systemically effective and therefore can also be used as foliar and soil fungicides.
  • fungi are suitable for controlling the following phytopathogenic fungi: Blumeria graminis (powdery mildew) Cereals, Erysiphe cichoracearum and Sphaerotheca fuliginea Cucurbitaceae, Podosphaera leucotricha on apples, Uncinula necator on vines, Puccinia species on cereals, Rhizoctonia species on cotton, rice and turf, Ustilago species on cereals and sugar cane, Venturia inaequalis (scab) on apples, Helminthosporium species on cereals, Septoria nodorum on wheat, Botrytis cinera (Gray mold) on strawberries, vegetables, ornamental plants and vines, Cercospora arachidicola on peanuts, Pseudocercosporella herpotrichoides on wheat and barley, Pyricularia oryzae on rice, Phytophthora infestans on potatoes and tomatoes, Plasmopara, viticola on
  • the compounds I and II are usually in a weight ratio from 100: 1 to 1:20, especially 80: 1 to 1: 1 applied.
  • the application rates of the mixtures according to the invention are especially on agricultural crops, depending on the type of crop Effects at 0.01 to 8 kg / ha, preferably 0.1 to 5 kg / ha, in particular 0.1 to 3.0 kg / ha.
  • the application rates are for the compounds I at 0.01 to 1 kg / ha, preferably 0.05 to 0.5 kg / ha, in particular 0.05 up to 0.3 kg / ha.
  • the application rates for compounds II are included accordingly 0.01 to 1 kg / ha, preferably 0.02 to 0.5 kg / ha, in particular 0.05 to 0.3 kg / ha.
  • Seed treatment generally involves application rates Mixture of 0.001 to 250 g / kg of seed, preferably 0.01 to 100 g / kg, in particular 0.01 to 50 g / kg used.
  • pathogenic harmful fungi are to be controlled for plants, takes place the separate or joint application of the compounds I and II or the mixtures of the compounds I and II Spraying or dusting the seeds, plants or soil before or after sowing the plants or before or after Emergence of the plants.
  • the compounds I and II may be in the form of directly sprayable solutions, powders and suspensions or in the form of high-percentage aqueous, oily or other suspensions, Dispersions, emulsions, oil dispersions, pastes, dusts, Streuschn or granules processed and by spraying, Nebulizing, dusting, scattering or pouring are applied.
  • the application form depends on the intended use; she should be in in each case the finest possible and even distribution of Ensure mixture according to the invention.
  • the formulations are prepared in a manner known per se, e.g. by adding solvents and / or carriers.
  • the Formulations are usually inert additives such as Emulsifying agent or dispersant admixed.
  • Surfactants are the alkali, alkaline earth, Ammonium salts of aromatic sulfonic acids, e.g. Lignin-, Phenol, naphthalene and dibutylnaphthalenesulfonic acid, and of Fatty acids, alkyl and alkylaryl sulfonates, alkyl, lauryl ether and fatty alcohol sulfates, as well as salts of sulfated hexa, hepta and octadecanols or fatty alcohol glycol ethers, condensation products sulfonated naphthalene and its derivatives with formaldehyde, Condensation of naphthalene or the Naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl, octyl or Nonylphenol, alkylphenol or tributylpheny
  • Powders and dusts can be mixed or mixed Grinding the compounds I or II or the mixture of the compounds I and II prepared with a solid carrier become.
  • Granules for example coated, impregnated or homogeneous granules
  • fillers or solid carriers serve, for example Mineral earths such as silica gel, silicic acids, silica gels, silicates, Talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, Diatomaceous earth, calcium and magnesium sulphate, magnesium oxide, ground plastics, as well as fertilizers such as ammonium sulphate, Ammonium phosphate, ammonium nitrate, ureas and vegetable products like cereal flour, tree bark, wood and nutshell flour, Cellulose powder or other solid carriers.
  • Mineral earths such as silica gel, silicic acids, silica gels, silicates, Talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, Diatomaceous earth, calcium and magnesium sulphate, magnesium oxide, ground plastics, as well as fertilizers such as ammonium sulphate, Ammonium phosphate, ammonium nitrate, urea
  • the formulations generally contain from 0.1 to 95% by weight, preferably 0.5 to 90% by weight of one of the compounds I or II or the mixture of the compounds I and II.
  • the active ingredients are in a purity of 90% to 100%, preferably 95% to 100% (by NMR or HPLC spectrum) used.
  • the use of the compounds I or II, the mixtures or the appropriate formulations are such that the harmful fungi, their habitat or the plants to be kept free of them, seeds, Floors, surfaces, materials or spaces with a fungicidal effective amount of the mixture, or of the compounds I and II separate application, treated.
  • the application may be before or after the infestation by the harmful fungi respectively.
  • the active ingredients were separated or together as a 10% emulsion in a mixture of 63% by weight of cyclohexanone and 27% by weight of emulsifier prepared and according to the desired concentration diluted with water.
  • the infestation corresponds to the treated Plants that of the untreated control plants; at an efficiency of 100, the treated plants had no Infested.
  • Leaves of pot fry of the variety "Müller-Thurgau” were sprayed to drip point with aqueous active ingredient preparation, which was prepared with a stock solution consisting of 10% active ingredient, 85% cyclohexanone and 5% emulsifier.
  • aqueous active ingredient preparation which was prepared with a stock solution consisting of 10% active ingredient, 85% cyclohexanone and 5% emulsifier.
  • the undersurfaces of the leaves were inoculated with an aqueous zoospore suspension of Plasmopara viticola.
  • the vines were first placed for 48 hours in a steam-saturated chamber at 24 ° C and then for 5 days in the greenhouse at temperatures between 20 and 30 ° C. After this time, the plants were again placed in a humid chamber for 16 hours to accelerate the sporangiopathic outbreak.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Claims (10)

  1. Mélanges fongicides, contenant
    A) des composés amide de la formule I
    Figure 00180001
       dans laquelle
    R1, R2
    sont identiques ou différents et représentent de l'halogène ou un groupe nitro, cyano, alkyle en C1-C8, alcényle en C2-C8, alcynyle en C2-C8, halogénoalkyle en C1-C8, halogénoalcényle en C2-C8, halogénoalcynyle en C2-C8, alcoxy en C1-C8, halogénoalcoxy en C1-C8, halogénoalkylthio en C1-C8, alkylsulfinyle en C1-C8 ou alkylsulfonyle en C1-C8,
    x
    vaut 1, 2, 3 ou 4,
    y
    vaut 1, 2, 3, 4 ou 5,
    et
    B) des dérivés d'imidazole de la formule II
    Figure 00190001
    dans laquelle R1 et R2 représentent de l'halogène ou du phényle qui peut être substitué par de l'halogène ou de l'alkyle en C1-C4, ou
    R1 et R2 forment conjointement avec la double liaison C=C formant pont un groupe 3, 4-difluorométhylènedioxyphényle,
    R3
    représente un groupe cyano ou de l'halogène, et
    R4
    représente un groupe di- (C1-C4-alkyl)-amino ou isoxazol-4-yle, qui peut porter 2 radicaux alkyle en C1-C4,
    en une quantité synergiquement efficace.
  2. Mélange fongicide suivant la revendication 1, dans lequel le dérivé d'imidazole II répond à la formule IIa
    Figure 00190002
  3. Mélange fongicide suivant la revendication 1, dans lequel le dérivé d'imidazole II répond à la formule IIb
    Figure 00200001
    où X représente du chlore ou du brome.
  4. Mélange fongicide suivant les revendications 1 à 3, caractérisé en ce que le rapport pondéral entre les composés amide I et les dérivés d'imidazole de la formule II est de 100/1 à 1/20.
  5. Procédé de lutte contre des champignons nuisibles, caractérisé en ce qu'on traite les champignons nuisibles, leur environnement ou les plantes, semences, sols, surfaces, matériaux ou espaces qui doivent en être libérés avec des composés amide de la formule I suivant la revendication I et des dérivés d'imidazole de la formule II suivant les revendications 1 à 3.
  6. Procédé suivant la revendication 5, caractérisé en ce qu'on répand des composés amide de la formule I suivant la revendication 1 et des dérivés d'imidazole de la formule II suivant les revendications 1 à 3 simultanément, et ce conjointement ou séparément ou successivement.
  7. Procédé suivant la revendication 5 ou 6, caractérisé en ce qu'on applique le composé amide de la formule I suivant la revendication 1 en une quantité de 0,01 à 2,5 kg/ha.
  8. Procédé suivant les revendications 5 à 7, caractérisé en ce qu'on applique les dérivés d'imidazole de la formule II suivant les revendications 1 à 3 en une quantité de 0,01 à 10 kg/ha.
  9. Utilisation des composés amide de la formule I suivant la revendication 1, pour la préparation d'un mélange synergique efficace du point de vue fongicide suivant la revendication 1.
  10. Utilisation des dérivés d'imidazole de la formule II suivant les revendications 1 à 3, pour la préparation d'un mélange synergique efficace du point de vue fongicide suivant la revendication 1.
EP01271095A 2000-12-18 2001-12-13 Melanges fongicides se basant sur des composes d'amide Expired - Lifetime EP1345493B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
SI200130458T SI1345493T1 (sl) 2000-12-18 2001-12-13 Fungicidne zmesi na osnovi amidnih spojin

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10063047 2000-12-18
DE10063047 2000-12-18
PCT/EP2001/014651 WO2002049435A1 (fr) 2000-12-18 2001-12-13 Melanges fongicides se basant sur des composes d'amide

Publications (2)

Publication Number Publication Date
EP1345493A1 EP1345493A1 (fr) 2003-09-24
EP1345493B1 true EP1345493B1 (fr) 2005-11-09

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ID=7667632

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EP01271095A Expired - Lifetime EP1345493B1 (fr) 2000-12-18 2001-12-13 Melanges fongicides se basant sur des composes d'amide

Country Status (23)

Country Link
US (1) US20040029930A1 (fr)
EP (1) EP1345493B1 (fr)
JP (1) JP3881310B2 (fr)
KR (1) KR20030059347A (fr)
CN (1) CN1481215A (fr)
AR (1) AR031934A1 (fr)
AT (1) ATE308885T1 (fr)
AU (1) AU2002216105A1 (fr)
BR (1) BR0116240A (fr)
CA (1) CA2431417A1 (fr)
CZ (1) CZ296907B6 (fr)
DE (1) DE50108039D1 (fr)
DK (1) DK1345493T3 (fr)
EA (1) EA005678B1 (fr)
EC (1) ECSP034690A (fr)
ES (1) ES2250301T3 (fr)
HU (1) HUP0302212A3 (fr)
MX (1) MXPA03004968A (fr)
NZ (1) NZ526902A (fr)
PL (1) PL365535A1 (fr)
SK (1) SK7632003A3 (fr)
WO (1) WO2002049435A1 (fr)
ZA (1) ZA200305512B (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1585390A1 (fr) * 2002-11-15 2005-10-19 Basf Aktiengesellschaft Melanges fongicides a base de derives d'imidazole
GB0230155D0 (en) 2002-12-24 2003-02-05 Syngenta Participations Ag Chemical compounds
CN103719090A (zh) * 2013-12-09 2014-04-16 江阴苏利化学股份有限公司 一种含有氰霜唑和啶酰菌胺的杀菌组合物
CN109476571B (zh) 2016-07-22 2020-06-19 沙特基础工业全球技术有限公司 双酚a的制备
CN107771812A (zh) * 2016-08-29 2018-03-09 南京华洲药业有限公司 一种含啶酰菌胺和氰霜唑的杀菌组合物及其应用

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1339133C (fr) * 1987-03-13 1997-07-29 Rikuo Nasu Derives de l'imidazole et compositions a base de ces derives pour l'elimination d'organismes nuisibles
HU217905B (hu) * 1992-01-29 2000-05-28 Basf Ag Karbamátok, ezeket hatóanyagként tartalmazó fungicid készítmények és eljárás alkalmazásukra, valamint a karbamátok intermedierjei
DE4423612A1 (de) * 1994-07-06 1996-01-11 Basf Ag 2-[(Dihydro)pyrazolyl-3'-oxymethylen]-anilide, Verfahren zu ihrer Herstelung und ihre Verwendung
DE4423613A1 (de) * 1994-07-06 1996-01-11 Basf Ag 2-[1',2',4'-Triazol-3'yloxymethylen]-anilide, Verfahren zu ihrer Herstellung und ihre Verwendung
HUP9802822A3 (en) * 1995-08-10 1999-04-28 Bayer Ag Halobenzimidazol derivatives, intermediates, preparation thereof and microbocide compositions containing these compounds as active ingredients
UA65600C2 (uk) * 1997-12-18 2004-04-15 Басф Акцієнгезелльшафт Фунгіцидна суміш на основі амідних сполук і похідних піридину

Also Published As

Publication number Publication date
US20040029930A1 (en) 2004-02-12
ES2250301T3 (es) 2006-04-16
DE50108039D1 (de) 2005-12-15
CN1481215A (zh) 2004-03-10
HUP0302212A3 (en) 2005-10-28
SK7632003A3 (en) 2003-11-04
AR031934A1 (es) 2003-10-08
BR0116240A (pt) 2004-01-06
ECSP034690A (es) 2003-09-24
CZ296907B6 (cs) 2006-07-12
ATE308885T1 (de) 2005-11-15
EP1345493A1 (fr) 2003-09-24
MXPA03004968A (es) 2003-09-05
ZA200305512B (en) 2004-08-27
JP3881310B2 (ja) 2007-02-14
HUP0302212A2 (hu) 2003-10-28
WO2002049435A1 (fr) 2002-06-27
JP2004516256A (ja) 2004-06-03
KR20030059347A (ko) 2003-07-07
AU2002216105A1 (en) 2002-07-01
PL365535A1 (en) 2005-01-10
EA200300670A1 (ru) 2003-12-25
EA005678B1 (ru) 2005-04-28
CZ20031661A3 (cs) 2003-09-17
DK1345493T3 (da) 2006-01-30
NZ526902A (en) 2005-03-24
CA2431417A1 (fr) 2002-06-27

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